Acetic Acid → HCID 67342865, compound

HRID 1669791Notes

Reaction equation

HRID 1669791 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[O:15]=[C:16]([CH3:25])[CH2:17][C:18]([O:20][CH2:21][CH:22]1[CH2:24][CH2:23]1)=[O:19].C(O)(=O)C.N1CCCCC1>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:17]([C:16](=[O:15])[CH3:25])[C:18]([O:20][CH2:21][CH:22]1[CH2:24][CH2:23]1)=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 10012135Cyclopropylmethyl 3-oxobutanoateHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 67342865HCID 67342865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (2.65 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 798 mg (2.65 mmol) of cyclopropylmethyl 3-oxobutanoate, 38 μl (0.66 mmol) of acetic acid and 66 μl (0.66 mmol) of piperidine in 25 ml of anhydrous dichloromethane are heated after addition of 4 Å molecular sieves (1.5 g) under reflux for 24 h. After cooling, the suspension is filtered with suction and the filtrate is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is purified by preparative HPLC. 650 mg (74% of theory) of the title compound are obtained as an E/Z mixture.

Workup

  1. additionafter addition of 4 Å molecular sieves (1.5 g)
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. filtrationthe suspension is filtered with suction
  5. washthe filtrate is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-c0904ffa10f4424cb02052c822ad7f87
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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